Polymer from aromatic diamine and N,N,N&#39;,N&#39;-tetraglycidyl-1,3-propylene bis(p-aminobenzoate)

ABSTRACT

Polymers of a polyfunctional epoxy compound, N,N,N&#39;,N&#39;-tetraglycidyl-1,3-propylene bis(p-aminobenzoate), formed by reaction of such epoxy compound with aromatic polyamines. The disclosed polymers are useful as structural resins, e.g., as advanced composite matrix resins.

This is a division of application Ser. No. 518,856 filed Aug. 1, 1983,now U.S. Pat. No. 4,518,786.

FIELD OF THE INVENTION

This invention relates to a new and useful compound. More particularly,it provides N,N,N',N'-tetraglycidyl-1,3-propylene bis(p-aminobenzoate)which is useful as an epoxide resin.

BACKGROUND OF THE INVENTION CROSS REFERENCE TO RELATED APPLICATIONS

This application is related to the following concurrently filedapplications:

    ______________________________________                                        Attorneys Docket                                                                         Serial No. Applicant(s)                                            ______________________________________                                        110-031 (28,954)                                                                         518,872    D. W. Wang, J. L. Courter,                                                    D. K. Kohli.                                            110-033 (29,457)                                                                         518,873    K. Hirschbuehler.                                       110-034 (29,054)                                                                         518,874    K. Hirschbuehler, D. K. Kohli.                          110-035 (29,458)                                                                         518,879    D. R. Draney, D. K. Kohli.                              ______________________________________                                    

DESCRIPTION OF THE PRIOR ART

Polyfunctional epoxy resins derived from aromatic polyamines are known,e.g., from U.K. Pat. No. 907,844, and they can be cured with aromaticpolyamines to form structural resins.

SUMMARY OF THE INVENTION

It has now been found that a tetraglycidyl derivative of 1,3-propanediolbis-(p-aminobenzoate), and its homopolymers, can be prepared, that ithas utility, for example, as an epoxy resin prepolymer, and that thepolyaddition products thereof with aromatic polyamines have advantageousproperties.

DESCRIPTION OF THE INVENTION

According to the present invention, there are providedN,N,N',N'-tetraglycidyl-1,3-propylene-bis(p-aminobenzoate), andhomopolymers thereof.

DESCRIPTION OF THE PREFERRED EMBODIMENT

The following example illustrates the preparation and demonstrates useof the compound of this invention, and its homopolymers.

EXAMPLE

1,3-propylene bis-(p-aminobenzoate), 314.34 g. (U.S. Pat. No. 3,932,360)is dissolved in a mixture comprising 1560 g. of epichlorohydrin, 500 ml.of ethanol, and 50 ml. of water at about 23° C., then the mixture isheated to 80° C. with stirring for 40 hours. Sodium hydroxide solution,400 g. of 50% by weight in water, is added dropwise over 45 min. duringwhich the temperature reaches 65° C. The temperature is subsequentlymaintained at 60°-65° C. for 4 hours. The liquid is decanted and thesolid is washed with methylene chloride. The combined filtrate andwashings are vacuum stripped at 65° C. to leave a viscous residue. Thisis dissolved in 500 ml. of CH₂ Cl₂, 250 ml. of H₂ O and 250 ml. ofmethyl isobutyl ketone. The organic layer is separated and washed withwater (3×500 ml.). The solution is dried with anhydrous magnesiumsulfate, filtered, and the solvent is vacuum stripped to a finaltemperature of 130° C. The product, a viscous oil, weighs 497 g., 92% oftheoretical. Epoxy equivalent weight is 152-153 g./epoxide group. Thecompound has the formula: ##STR1##

Mixing the compound at a ratio of 1.0 epoxide equivalents with 0.75NH-amine equivalents of, respectively, diaminodiphenyl sulfone(Composition A) and 1,3-propanediol bis-(p-aminobenzoate) (CompositionB) at 110°-130° C. and then curing the mixtures at 135°-180° C. providedspecimens for flexural testing in accordance with ASTM D-790, Method 1.The results were as follows:

    ______________________________________                                        Composition       A      B                                                    ______________________________________                                        Modulus MSI       0.58   0.57                                                 Strength KSI      22.7   23.4                                                 Strain, %         4.4    5.6                                                  ______________________________________                                    

The foregoing properties typify advanced composite matrix resins.

The above-mentioned patents and publications (ASTM methods) areincorporated by reference. Obvious variations providing the samefunctional advantages are within the full intended scope of the appendedclaim.

What is claimed is:
 1. The resinous polymer fromN,N,N',N'-tetraglycidyl-1,3-propylene bis(p-aminobenzoate) and anaromatic polyamine.
 2. The resinous polymer of claim 1, wherein saidaromatic polyamine is selected from the group consisting ofdiaminodiphenyl sulfone and 1,3 propanediol bis-(p-aminobenzoate).